To clarify, it's Paul who bought and gets service done at LOTO - my dealer's in Topeka.
There's no problem with getting the boat delivered to TR, you'll just have to work out the cost & scheduling with the dealer, whoever that is. The only real issue could be that if for any reason you need warranty service, the selling dealer is somewhat reasonable in expecting the boat to be taken to their place for the analysis and any repair work. As you know there are no FW dealers at TR (a fact that has always amazed me). If you know of a Volvo Penta certified shop nearby, I frankly recommend you go with Volvo. If not, you'll save yourself some headaches with Merc. Either way, drive train warranty issues are separate from all other issues - if you have a fiberglass problem, upholstery, electrical, etc., your FW dealer is probably going to want you to deliver the boat to them for the work. Hence the fact that 98% of the boats at TR are Crownlines, since they seem to have a monopoly on dealers there.
Generally the rule of thumb on Merc vs Volvo is to go with whatever is easiest to get serviced in your area. For anywhere in MO, that usually means Merc. And that's all I have to say about that

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I'm the last one qualified to opine on the other boats you're considering, other than to say they're all great brands and great quality. I recommend you sea trial as many of your candidates as possible before jumping head first into what is a pretty large boat for a first-time buyer. There are many subtle things you'll notice (and possibly dislike) about any given model that you'll never see until you're on the water with it. We were ready to put a deposit down on a Funship until we actually drove it, and discovered that the top edge of the windshield fell directly in the center of my line of sight. It didn't do that sitting on the trailer.
While this isn't the most comfortable time of year to drive a boat, we were sea trialing them at LOTO in March with our coats on, it can be done.
I echo Cougar's sentiments on the discounts. In '05 we did 24% off MSRP plus they paid for the extended warranty, although that was through a VERY low overhead dealer (which is not the case with the LOTO dealer, however). But the bigger boat and the 2fer should gain you some real buying power. Just make sure you're getting what you want, and that all the transportation and warranty service expectations are understood.
I'm not familiar with the Emerald Point area, but it seems like we've driven by Big Cedar Lodge (or maybe I just remember the name from looking up places to stay on the net). We've thought about buying into a condo there, but don't think we're quite to that point yet (teenagers with issues

).